Pet-friendly holiday rentals in Dutchess County

we stayed at Garrett's while attending a retreat at Omega. it's a beautiful little home on a gorgeous property. very comfortable and clean, it is a very charming space.

My wife and I had a great time. Amazing house right outside of town. Huge yard which our dog loved! Hopefully we will be back.

It was a great stay and Vince was a great host. Everything was taken care of and the house had everything we would need, especially for cooking and grilling. The pullout beds are a little old but there are plenty of bed spots and places to sleep. Great weekend spot for a big group.

The place was clean and exactly as described. On the good weather days, it was nice to be close to some hikes and restaurants. On the rainy days, we enjoyed how cozy the space was.

Simply put, this is one of the most beautiful homes I’ve ever set foot in—let alone had the privilege of staying in. From the moment we arrived, it was clear this space had been curated with intention, soul, and an impeccable eye for detail. The interiors strike that rare balance between feeling thoughtfully designed and effortlessly lived-in. Every corner offers something to admire: richly layered textures, perfectly chosen art, and a harmonious flow that invites both connection and rest. The outdoor spaces are just as stunning—landscaping that feels native yet refined, with spaces for gathering, lounging, and simply taking in the natural beauty that surrounds you. Inside, the comfort is next-level. The beds were deeply restorative (think luxurious, cloud-soft linens). We felt wrapped in calm the entire weekend. It’s rare to stay somewhere that feels this special — equal parts sanctuary, design inspiration, and joyful retreat. I already can’t wait to return 🪩

What a perfect place to stay! We were very comfortable in Hazel’s little retreat… we slept well in the king sized bed, had plenty of hot water, loved the bucolic green space and the creek nearby. Our dogs had great walks under the canopy of huge trees surrounding the property. I especially enjoyed watching and hearing the ducks, geese and swans across the street as they paddled to the pond! Thank you, Hunter for providing a perfect getaway spot for your guests!

We had a wonderful stay at Barbara’s place. Location is excellent, with amazing access to nature, walking distance to the Hudson River Brickyard Trail, Kingston Point Beach, the Rail Trail, and a nearby dog run. The house itself was spotless and thoughtfully stocked with everything we needed, which we really appreciated (especially since so many Airbnbs can feel a bit bare). The space is also filled with books and art—you can tell Barbara put a lot of care into curating it. It felt like home right away. And to top it off, aside from the proximity to great walks, Barbara also provided a dog bed, bowls, ball, poo bags to make us feel truly welcome to have our dog with us. This was something we'd never experienced before. Thanks again Barbara!

What we look for in a property are that it is clean, comfortable and in a nice location. This checked the boxes. We had a wonderful four-night stay in June at this charming historic home with a nice view of the Hudson. Eve was a fantastic host! Her communication was clear and responsive before and throughout our visit. The location is ideal for exploring the area: walkable to the Vanderbilt estate and directly on the Hyde Park trail system for scenic walks. If you prefer to drive, it’s just minutes from the FDR Library and Home, Eleanor Roosevelt’s Val-Kill, the Mills Mansion, and the Culinary Institute of America. This is an older home and it is cozy and welcoming, with an incredible book collection and a beautiful upper porch overlooking the Hudson which is perfect for morning coffee or evening drinks. Would 100% stay again and hope to make it back in the future. Thank you for a lovely stay!

Craig’s place was great! Bedrooms were a good size and beds were very comfortable. Nice open living space. Beautiful grounds. Everything was clean and we had whatever we needed in the kitchen. Very private and quiet location. Would definitely stay again!

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Peaceful and charming stay in Rhinebeck. The farmhouse was cozy, and the kids loved watching the goats and turkeys roam. A perfect little reset while antiquing.

Blake is a kind and attentive host. The house is fun and eclectic. Many interesting things to look at, art books to leaf through and she has a great record album collection. It has all the necessities you would hope to see in an airbandb. I like the location. We enjoyed taking a hike in Mount Beacon park to see the remnants of an old casino and great views of the Hudson Valley.

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.

Beautiful place with lovely views. Close to lots of restaurants, hikes, parks, and quaint villages. Plenty of room for our extended family.

Really clean and well thought out B&B. Very quit surroundings. Would gladly stay again.

Our stay at Kyles guesthouse was wonderful, and we would definitely return. If you’re looking to escape into beautiful serene scenery away from the hustle and bustle this is it! Lots to do in the surrounding areas, but it’s wonderful to return to the peace and quiet of this airbnb. The accommodations were great and just as described. The only thing I’d note is that the guesthouse is attached to the main house, and so noise travels. Nothing that bothered us, but something to note if that’s something you care about. Anyway, I definitely recommend staying here!

It was a great stay and beautiful home. Really appreciated the ease of entry and amazing scenery.

Perfect relaxing getaway to extend our wedding weekend upstate. Thank you so much!

Stayed here with friends and family for my husband's art opening at Wassaic Project. The location was perfect! Design style of the house was perfect for us and the main kitchen/gathering space was gorgeous. Bedrooms were wonderful, especially the primary with the outdoor shower off the bathroom. We enjoyed two meals on the deck and had more than enough room to spread out in different areas of the home. Each bedroom opened to the deck, which was lovely. Kitchen was the most stocked I've ever experience in any Airbnb. Tons of attention to detail, including the art and extra comfy Parachute linens. It did get a little toasty for us upstairs when we were cooking in the evening but cooled off in the with the deck doors open. We all agreed to a return trip in the future! Just a lovely experience.

Lots of space. Appreciated that we could bring our cat. The electric fireplace was a nice touch especially since the weather for May was cold and rainy. All the amenities were provided for a nice stay. Check out the Center for Performing Arts for a show during your stay. That was a nice bonus.

This is a lovely stay nestled in the heart of Dutchess County. It is a short drive to Millbrook and not too far to Poughkeepsie and other surrounding towns. The home was clean and well kept. It has all the items you may need. The yard and spacious and surrounded by mature nature on a quiet road. An alpaca farm is just up the road and Zoe's Ice Cream Barn is around the corner. We would surely stay here again.

In a simple word… terrific! Cornelia’s place was wonderful! It was very clean, updated, private and welcoming! I would HIGHLY recommend staying here if you are in the area. Excellent host & property!

Max and Emily, we truly loved staying at your barn. Spacious, comfortable and lovely. And you obviously enjoy being hosts, the extras - fresh eggs, snacks, bottled water, and doing all of the cleaning prep (?!)make that obvious! We'd want to stay here if we're in the area again. Thanks again, you're terrific!